Abstract:
Synthesis, characterization and biological activity of ferrocenyl derivatives:
Study of the effect of different core moieties and substituents on anticancer and antioxidant activity
Montes-González, Ingrid1, Delgado-Rivera, Sara M.1; Henríquez-López, Sebastián A.1; Pérez-Ortiz, Giovanny E.1; Baerga-Ortiz, Abel2; Piñero-Cruz, Dalice M.1
1Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, San Juan, PR 00931
2 Department of Biochemistry, University of Puerto Rico, Medical Sciences Campus, San Juan, PR
Cancer is the second cause of death in the United States reported by the World Health Organization. Many researches are focused on different analogues for the design and development of novel and more potent drug. Chalcones, stilbenes and aromatic ethyne scaffolds show multiple biological and medicinal properties, including anti-cancer potential. Moreover, it is documented that the incorporation of the ferrocene moiety as a bioisostere in these scaffolds could improve their bioavailability and biological activity. Our research group focuses on the synthesis and characterization of various ferrocenyl compounds with different cores: chalcone, stilbene, and ethyne and explore their biological applications. The effect of different substituents in the phenyl group like amino, nitro, methoxy, fluorine, methylpyridinium, among others, is also studied. These derivatives have been synthesized employing well-known synthetic methodologies such as Claisen-Schmidt, Sonogashira, and Heck reactions with moderate to good yields (35%- 99%) and applying a greener approach when possible. Once compounds are synthesized and characterized, their biological activity is studied against some cancer cell lines such as MDA-MB-231, PC-3, HeLa, among others. Also, the radical scavenging properties of the compounds were explored by determining their potential as antioxidants using DPPH assay. We correlate some trends of different ferrocenyl cores and substituents with their biological activity results and apply these findings in the design of new drugs to treat cancer disease containing ferrocenyl moiety. The synthesis, characterization, biological assays results and the trends shown by these compounds will be elaborated and its implementation on the undergraduate organic laboratory course.
BIO:
Ingrid Montes has been a professor at the University of Puerto Rico at Río Piedras for 34 years. She has two current areas of research: Organometallic chemistry and chemical education. In the organometallic chemistry area, she explores the synthesis and characterization of various ferrocene derivatives and studies their potential applications, such as, polymers, photovoltaic cells, and drug design. She develops new methodologies applying green chemistry principles. In chemical education, her research work is based upon the theoretical perspective, building on constructivist learning theory, applied to organic chemistry, green chemistry and history of chemistry learning. She is proud to have directed the research of more than one hundreds of undergraduate and graduate students in Puerto Rico, all of whom have gone on to successful academic, professional, and industrial careers. Through her research and volunteer service she has contributions to Chemistry, Chemical Education, and Community outreach in Puerto Rico, Latin America, and the world.
Dr. Montes has been extremely active at the national, state and local level of chemistry, active in leadership, governance, and programming. Since 2013, she is Director-at-Large, Board of Directors, American Chemical Society (ACS), Chair of the Committee of Professional and Member Relations of the Board of Directors, Board’s Liaison to globalization (2018–19). She is the founder of the Chemistry Festival, adopted in 2015 as an ACS program. This program is now international, and more than 50 Festivals have been held around the world and over 60,000 people have been impacted. She is also co-founder and coordinator for the Spanish webinar series of the American Chemical Society and Mexican Chemical Society. She is a member of the Editorial Advisory Board for the Journal of Chemical Education; she was the Chair of the Theme Team for the ACS International Year of Chemistry (2011); Chair of the ACS Committee on Community Activities; Chair of the Advisory Board for ChemMatters Magazine; and a member of the Society Committee on Chemical Education (SOCED), among others. Dr. Montes was a member of the IUPAC 2011 Organizing Committee, including Chair of their Outreach Committee for the 2011 Meeting held in Puerto Rico. She was one of the Keynote speakers at the International Conference on “New Directions in Teaching, Learning and Evaluation of chemical Sciences at Tertiary Level” held in Sri Lanka. At a local level, she had been a member of the Board of Directors of the ACS-Puerto Rico Section for 26 years. Her roles include among others, being the Chair for three times, (1995, 2003, 2011), Councilor (1998 to 2013), Outreach coordinator and SEED Program Coordinator. In her Institution, she had occupied some administrative positions as being the Associate Dean for graduate studies of research-College of Natural Sciences and had chaired many committees at the UPR System, Campus, College of Natural Sciences, and Departmental level including chairs the system-wide committee of the University of Puerto Rico that oversees the improvement of academic chemistry programs.
For the past 31 years, Dr. Montes has been the Faculty Advisor of the ACS, Student Member’s Chapter. This chapter has received 27 consecutive ACS Student Outstanding Awards and has been recognized as Green Chapter since its establishment. These positions have enabled her to mentor and inspire thousands of underrepresented students, most specifically Hispanic women. As a long-time educator, her philosophy is to assist students in their career development by encouraging networking, teamwork, effective communication, and critical thinking. In addition to this role, she strongly believes in the development of students’ character and leadership by encouraging strong work ethics, service awareness and building self-esteem and self-insight. Together, this combination and foundation help instill and inspire integrity, and a better overall technical professional development.
Dr. Montes is an American Chemical Society and IUPAC (International Pure and Applied Chemistry) Fellow. In 2017, she was selected as one of the twelve IUPAC 2017 Distinguished Women in Chemistry or Chemical Engineering of the world. She deserved 2012 ACS Volunteer Service Award, since 2013, Honorary Member, Golden Key International Honour Society, and has received many recognitions In Puerto Rico, USA and internationally.
Dr. Montes is an author/co-author of Laboratory Manuals for teaching chemistry, contributor of various book chapters, over 300 presentations (invited or coauthored with her students), and various refereed publications over her distinguished career as both an educator and a researcher.